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<h1><a href="https://archiveofourown.org/works/23305231">Anchors Up</a> by <a class='authorlink' href='https://archiveofourown.org/users/WorldOfDemons/pseuds/WorldOfDemons'>WorldOfDemons</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>AU, Gen, Pirate AU, possible deanxreader - Freeform</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>In-Progress</td></tr>

<tr><td><b>Published:</b></td><td>2020-03-25</td></tr>

<tr><td><b>Updated:</b></td><td>2020-03-24</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-01 13:29:08</td></tr>

<tr><td><b>Rating:</b></td><td>Teen And Up Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>Creator Chose Not To Use Archive Warnings</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>2,165</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/23305231</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/WorldOfDemons/pseuds/WorldOfDemons</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>You're the captain of the Adelaide and have competition from a new crew as you plan for an attack.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>possible deanxreader</td></tr>

<tr><td><b>Comments:</b></td><td>1</td></tr>

<tr><td><b>Kudos:</b></td><td>2</td></tr>

</table>

<a name="section0001"><h2>Anchors Up</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Hello, have the results of quarantine. <br/>I don't think everything is perfectly historical, but it's mostly accurate. If I continue it I'll be doing more research. <br/>I'm not promising more, but I have a couple of ideas so the option is there and open for me. &lt;3</p>
    </blockquote></div><div class="userstuff module">
    
    <p>
  <br/>
  <br/>
  <br/>
</p><p>
  <span>The storm came out of nowhere. I clung to the wheel desperately trying to hold the course. Just the night before the blinking lights of Port Royal had been spotted. The storm had been gathering on the horizon.  I had hoped to get to shore before a hurricane hit, but it wasn’t meant to be.  </span>
</p><p> </p><p>
  <span>“Mr. Novak, take the helm” I shouted over the roar of the churning ocean. Some of the weight was lifted from my shoulders as Castiel helped hold the massive wheel. My boots slipped as rainwater soaked the wood planks. I had weathered worse storms than this but under the head of my father, not my own leadership. </span>
</p><p> </p><p>
  <span>“Have you tried pulling down your top, Captain, a woman’s breasts calm the seas” Benny called out from halfway up the rigging. I could practically hear the grin in his voice. The crazy bastard loved when the seas were rough. </span>
</p><p> </p><p>
  <span>“Watch your mouth, Lafitte, or I’ll toss you overboard myself,” I retorted, still straining against the weight. It felt like hours for the winds to finally calm. I was drenched from head to toe along with everyone else on the crew, but the sun was finally shining again. Most of the crew were saying their prayers thanking whatever God they praised for seeing the ship through the storm. I was more concerned with getting everyone safely into port. God could wait his turn for my attention. </span>
</p><p>
  <br/>
  <br/>
  <br/>
</p><p>
  <span>The crew was drunk. There’s no way around the fact as I sat at the bar and watched them. I nursed my mug of ale trying to keep an eye on them. Not that I’d do much of anything if they got themselves in trouble. If they wanted to get stabbed in a bar brawl that was their business. Just as long as they were ready to sail in the morning.</span>
</p><p> </p><p>
  <span> As soon as we docked my contact was waiting to unload the goods. Stolen goods, but Master Crowley didn’t care how the Spanish gold ended up in his hands, as long as it was shiny, he didn’t discriminate. Gold was traded for rum and food with a little cash left for the pubs and the women therein. </span>
</p><p> </p><p>
  <span>I glanced to my right as Castiel sat down on the bench next to me. </span>
</p><p> </p><p>
  <span>“So what’s our next heading, Captain?” he asked as I took another drag from my cup. </span>
</p><p> </p><p>
  <span>“I heard a rumor there’s a Dutch ship going to Nassau,” I answered and he nodded. </span>
</p><p> </p><p>
  <span>“I heard the same rumor, but I also heard that another crew may be pursuing it as well.” I mulled over the new information and came to my conclusion with a small smile. </span>
</p><p> </p><p>
  <span>“Then I suppose we’ll just have to be faster.” </span>
</p><p>
  <br/>
  <br/>
</p><p>
  <span>The younger half of the crew were groaning and puking the next day with the others laughing. They had all been there, paid their dues, and knew how to handle their drink. Adam, in particular, was looking green and we hadn’t even gotten out of the shallows yet. </span>
</p><p> </p><p>
  <span>“Shall we cast off, Captain?” Castiel joined me at the rails as the last casks were loaded below deck. I glanced down along the docks. </span>
</p><p> </p><p>
  <span>“Soon, Mr. Novak, soon. Do you see that ship about 3 down from us?” I asked. I had known almost everyone in this port for as long as I had been on the seas. Most of the crews had watched me grow up from running across decks while in port with Father and taking over </span>
  <em>
    <span>Adelaide </span>
  </em>
  <span>after he died. </span>
</p><p> </p><p>
  <span>“Yes, that would be the </span>
  <em>
    <span>Mary</span>
  </em>
  <span>,” Castiel answered and I knew exactly his tone. </span>
</p><p> </p><p>
  <span>“Our competition?” I confirmed and didn’t need to look at him to sense his nod. </span>
</p><p> </p><p>
  <span>“Well, let’s see how fast little Mary is,” I tried to keep the smirk from my face, I tried. “Alright, boys, anchors up!” </span>
</p><p>
  <br/>
  <br/>
  <br/>
</p><p>
  <span>Little </span>
  <em>
    <span>Mary </span>
  </em>
  <span>was faster than I thought. We left several hours before her, but she was gaining fast. She’d reach Nassau before us, and the Dutch ship docked there if we didn’t get knots behind us and fast. </span>
</p><p> </p><p>
  <span>Nassau was slowly starting to appear on the horizon as I tried to ignore the quickly growing ship behind us. </span>
</p><p> </p><p>
  <span>“Ship dead ahead” a voice called from the crow’s nest above us. I pulled out my spyglass and peered over the waves. Sure enough, a ship flying Dutch East India Trading Company colors. </span>
</p><p> </p><p>
  <span>“Steady on,” I ordered, giving a glance back to </span>
  <em>
    <span>Mary</span>
  </em>
  <span>. She was still gaining, but not quite enough. By the time I gave the command to prepare to board, we were close enough to the Dutch ship to hear their near frantic shouts of confusion. Were we friends or foes?  </span>
</p><p> </p><p>
  <span>“How silly of me, they don’t recognize us. Mr. Novak, raise our colors.” A black flag was raised up our previously unadorned mast. Our identity was unmistakable. We were upon the ship before they had a full understanding of what was happening. I could hear the shouts, warning of pirates and the scrambling to find weapons. The crew looked to me expectantly as we aligned with their side. With a nod from me and shouts from them, we boarded the </span>
  <em>
    <span>Batavia</span>
  </em>
  <span>. </span>
</p><p> </p><p>
  <span>It was a short skirmish, not even a battle. After only ten minutes of fighting, their crew was kneeling on deck with a plank stretching across the rails. Half my men were keeping an eye on the Dutch crew and the others were carrying the cargo to the </span>
  <em>
    <span>Adalaide</span>
  </em>
  <span>. </span>
</p><p> </p><p>
  <span>“You will be caught,” the Captain said from his knees. Ash rifled through the captain’s jacket and found a small bag of gold which he tossed my way. </span>
</p><p> </p><p>
  <span>“Not likely,” I answered flatly catching the bag. I was more concerned with </span>
  <em>
    <span>Mary</span>
  </em>
  <span> now nervously close. We didn’t have many injuries from the skirmish, but I’d rather not engage twice in one day. </span>
</p><p> </p><p>
  <span>“Alright, boys, let’s get some space between us and here,” I called before making my way over. It was time to embrace the oldest pirate tradition: running away. </span>
</p><p> </p><p>
  <span>Castiel stayed below deck taking stock of our plunder while I focused on making our escape. The most obvious route was to go the way we came, east of Cuba and around to Port Royal. But that would be obvious. If </span>
  <em>
    <span>Mary</span>
  </em>
  <span> had followed us from Jamacia, they’d be expecting us to return to Jamacia. We could trade in Havana before setting out again. That could work. </span>
</p><p> </p><p>
  <span>Little </span>
  <em>
    <span>Mary </span>
  </em>
  <span>may have been fast, but she didn’t know the Caribbean as I did. We managed to lose her west of the Bahamas and we made port in Havana. The Dutch cargo was sold off resulting in a hefty bag of gold on my desk as I made careful notes in the ledger. I tossed the bag to Castiel who stood at the door of my cabin. </span>
</p><p> </p><p>
  <span>“I’ve already taken out what we need to restock the ship, the rest can be split for the crew,” I barely looked up at him, still writing. I finished the list of things we needed to get and stuck it in my jacket pocket. </span>
</p><p> </p><p>
  <span>“And how long do they have to squander it?” he asked, trace amounts of humor in his voice. </span>
</p><p> </p><p>
  <span>“Let’s say three days, then we’ll head for Port Royal and see what other trouble we can get into. Hopefully, I can pay off Crowley for another lead.” </span>
</p><p>
  <br/>
  <br/>
  <br/>
  <br/>
</p><p>
  <span>I had hoped once we were out of sight, our pursuers would give up or start chasing someone else. At very least I expected for us to be off Cuba before they caught up. Unfortunately, we had no such luck. By our second day in Havana, </span>
  <em>
    <span>Mary</span>
  </em>
  <span> made port. Most of my crew had gathered in our usual haunt with myself and Castiel taking up residency of a table in the corner. A shattered bottle made the tavern go quiet. </span>
</p><p> </p><p>
  <span>“We’re looking for the crew of the </span>
  <em>
    <span>Adelaide,” </span>
  </em>
  <span>one of the men announced. I looked him over and leaned to Castiel. </span>
</p><p>
  <span>
    <br/>
  </span>
  <span>“Captain?” I asked and he nodded. </span>
</p><p> </p><p>
  <span>“Winchester,” he answered, “and the First Mate is his brother.” I took note of a taller man with long hair tied back. Most of the crew had gathered outside the tavern by the sound of it. </span>
</p><p> </p><p>
  <span>Lafitte threw back the last of his drink before slamming it on the bar. </span>
</p><p> </p><p>
  <span>“Well, you found us. Now what?” he challenged standing. A few others stood with him and I carefully watched both my crew and the tavern keeper. The last thing I wanted was to be forcefully thrown from the tavern. The keeper didn’t seem to care much, he had probably seen worse than what was to come. </span>
</p><p> </p><p>
  <span>“Are you planning on stopping them?” Castiel leaned in and asked as both crews started rumbling insults to the other. I sighed and pushed myself out of the chair. </span>
</p><p> </p><p>
  <span>“I suppose so, though if Lafitte gets shot it’s his own fault.” I slowly made my way to the back of my crew and smacked a few across the back of the head. </span>
</p><p> </p><p>
  <span>“Okay, out, out” I grabbed Adam by the collar and shoved everyone through the crowd around the door. I gave them a push down the street. </span>
</p><p> </p><p>
  <span>“Go, I’ll meet you on deck,” I gave Lafitte another push as he tried to protest. “Go, that’s an order.” I didn’t wait for him to continue protesting before slamming the door and facing Winchester. </span>
</p><p> </p><p>
  <span>“First of all, who are you and second what do you want with the </span>
  <em>
    <span>Adelaide</span>
  </em>
  <span>?” I asked sizing him up while also searching for Castiel now standing in the back of the tavern. </span>
</p><p> </p><p>
  <span>“I’m looking for the captain, where is he?” Winchester demanded, making me want to roll my eyes more than anything. </span>
</p><p> </p><p>
  <span>“You’re looking at her, now answer my questions if you want to start a fight with my crew,” I spat back not giving him the satisfaction of me fumbling over my words. It wasn’t the first time I had been questioned and it wouldn’t be the last. His brows furrowed in confusion as he took me in eventually disregarding any conflict he was fighting with. </span>
</p><p> </p><p>
  <span>“You stole our mark,” he accused and I scoffed resisting the urge to roll my eyes. </span>
</p><p> </p><p>
  <span>“So that was your ship? You don’t sound Dutch,” I decided to toy with him a bit. He was obviously new to the seas if he was trying to stake claims over marks. </span>
</p><p> </p><p>
  <span>“You knew we were going after that ship,” and I shrugged. </span>
</p><p> </p><p>
  <span>“And we got there first. Word to the wise, you’ll have to be faster next time if you want to make it out here,” I finished only infuriating him more. “There aren’t rules out here, and the ones we do have are really more guidelines.” I caught Castiel’s eyes and with a nod, I slipped out the door leaving a very angry pirate in my wake. </span>
</p><p>
  <br/>
  <br/>
  <br/>
</p><p>
  <span>The crew wasn’t happy about their fight being broken up, but that last thing I wanted to deal with was arrests. I let them air their grievances before bringing up that we were planning on leaving with the sunrise and I didn’t have time or money to get them out of jail. Once they were thinking with their brains and not their dicks, we all hunkered in for the last night in port. Usually, this would be spent getting as drunk as possible, but the mood across the entire ship was tense. </span>
</p><p> </p><p>
  <span>Everyone settled in below deck eventually leaving me alone on deck too alert to sleep. I’d rest easier once we were on the sea again. </span>
</p><p> </p><p>
  <span>“How did you become captain?” a familiar voice asked from the port deck. I glanced down from my perch on the railing. I debating answering, but there wasn’t malice in his voice at all. He had calmed down significantly. </span>
</p><p> </p><p>
  <span>“My father was the first captain and I literally grew up here. If you think learning to walk on land was hard, try the open ocean. I learned to work every position on this ship. He died about 5 years ago and left me in command. The crew didn’t protest and here I am.” I summed up my story in a few sentences. Winchester nodded kicking at the boards. </span>
</p><p> </p><p>
  <span>“Do I pass muster?” I asked trying to keep the mocking from my voice and he shrugged. </span>
</p><p> </p><p>
  <span>“Did you hear there’s an English Galleon on it’s way to Hispaniola?” he asked and my eyes squinted down at him. Why would he tell me valuable information like that? A full galleon was the prize of a lifetime. Even in the dull light, he must have seen me trying to work out what his thought process was. </span>
</p><p> </p><p>
  <span>“Friendly competition?” he suggested and I cocked my head suggesting it. I knew we were ready to set off as soon as the sun was up. It was a gamble, beating them, but maybe one worth taking. </span>
</p><p> </p><p>
  <span>“Okay, Captain Winchester. We’ll show you the way to Hispaniola. Wouldn’t want you to get lost,” I accepted the challenge with a grin. </span>
</p>
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